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Stereoselective Synthesis of Chiral α‐Amino‐β‐Lactams through Palladium(II)‐Catalyzed Sequential Monoarylation/Amidation of C(sp 3 )H Bonds
Author(s) -
Zhang Qi,
Chen Kai,
Rao Weihao,
Zhang Yuejun,
Chen FaJie,
Shi BingFeng
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306625
Subject(s) - palladium , intramolecular force , chemistry , stereoselectivity , catalysis , aryl , stereochemistry , derivative (finance) , functional group , medicinal chemistry , lactam , organic chemistry , alkyl , polymer , financial economics , economics
Give Me an Ar, give Me an N ! Arylation of the methyl group in a simple derivative of readily available alanine under palladium catalysis was followed by intramolecular amidation at the same position to give chiral α‐amino‐β‐lactams with a wide range of aryl substituents (see scheme; Phth=phthaloyl). The α‐amino‐β‐lactams were obtained in moderate to high yields with good functional‐group tolerance and high diastereoselectivity.